Hydrochloric Acid → HCID 67273452, compound

HRID 600620Notes

Reaction equation

HRID 600620 reaction equation
CON(C)[C:4]([C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][N:9]2[CH:15]=1)=[O:5].[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Mg]Cl.Cl.O>C1COCC1.C(OCC)C.C(OCC)(=O)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]2[N:9]([CH:15]=[C:6]([C:4]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH3:17])=[O:5])[N:7]=2)[CH:10]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 44124031HCID 44124031, compoundHCID 178424304HCID 178424304, compound

Product 1

HCID 67273452HCID 67273452, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-4 °C

Procedure

To a solution of 0.144 g of N-methoxy-N-methyl-6-chloroimidazo[1,2-a]pyridine-2-carboxamide in 3 mL of THF cooled to −4° C. is added dropwise a solution of 1.5 mL of a 2M solution of 2-methylphenylmagnesium chloride in ethyl ether. The reaction mixture is stirred for 3 hours at −4° C. 3 mL of 1N hydrochloric acid, 8 mL of water and 40 mL of ethyl acetate are added. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered, evaporated to dryness under reduced pressure, and then purified on a column of silica, eluting with a 90/10 mixture by volume of dichloromethane and ethyl acetate. The fractions containing the product are combined and concentrated to dryness under reduced pressure to give 0.034 g of (6-chloroimidazo[1,2-a]pyridin-2-yl)(2-methylphenyl)methanone in the form of a white solid.

Workup

  1. customAfter separation of the phases
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure
  5. custompurified on a column of silica
  6. washeluting with a 90/10 mixture by volume of dichloromethane and ethyl acetate
  7. additionThe fractions containing the product
  8. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ad26883a260a451ea59f800f01ba734b
Source dataset
uspto-grants-2011_03
Patent number
US07902219B2

Reaction notes

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